Longest losing streak for a county.

[Vosem]

Holmes County is a Thurmond '48-Stevenson '52-unpledged '56-unpledged '60-Goldwater '64-Humphrey '68-McGovern '72 county.

If you want to stick to just major-parties, there is a segment of southwestern Ohio that voted Greeley/Tilden/Hancock/Blaine/Cleveland, including Montgomery County (Dayton). It is really hard to find a modern example of a county voting for five different-party non-third-party losers consecutively, though Washtenaw County, Michigan, came very close in the 1970s and 1980s; it just barely voted Reagan '84, though. Had it not, it would have been McGovern/Ford/Carter/Mondale/Dukakis, but it was not to be.

If you want to stick to counties that always vote for popular vote losers, there are five contiguous counties in eastern Kentucky that voted Bush '00/Kerry '04/GOP since then, so they have now voted for PV losers in six consecutive elections.